The present invention relates to a cyclic azine dye and an electroluminescence (EL) device using the same.
At the present time, development and study on various display devices are aggressively driven. In particular, organic EL devices can obtain high luminance light emission at a low voltage and accordingly, are drawing an attention as a promising display device. For example, an EL device comprising an organic thin film formed by depositing an organic compound is known (see, Applied Physics Letters, Vol. 51, page 913 (1987)). The organic EL device described in this publication has a laminate structure comprising an electron transporting material and a hole transporting material and is greatly improved in the light emission properties as compared with conventional single-layer devices.
As a means to improve the light emission efficiency of the laminate-type EL device, a method of doping a fluorescent dye is known. For example, an organic EL device having doped therein a coumarin dye described in Journal of Applied Physics, Vol. 65, page 3,610 (1989) is greatly improved in the light emission efficiency as compared with non-doped devices.
Furthermore, by doping a fluorescent dye, light having a desired wavelength can be taken out. In order to apply the organic EL device to a full color display or back light, a fluorescent dye capable of emitting light at an appropriate wavelength and having excellent durability must be developed, in particular, a red fluorescent dye is being demanded in view of durability and light emission efficiency.
As the red fluorescent dye used in the organic electroluminescence device, 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyrane (DCM), for example, is doped and thereby emission of red orange light is obtained, however, this dye has problems that the color purity is low and the durability is poor, and cannot be used in practice. Neil Red is also known, however, this is still disadvantageous in that the color hue is short wave and the durability is not sufficiently high. In the same way, various EL devices which can emit light at a longer wavelength than the green light as a result of doping a fluorescent material have been developed, however, these devices all have serious problems that the color purity is low as red color light emission and the luminance of emitted light is not sufficiently high. EL devices using a conventional red fluorescent dye have another problem that the durability is low. Furthermore, with respect to a fluorescent dye which emits light in the blue green area, dyes capable of emitting light with excellent luminance and having superior durability have not yet been developed and a new dye is being demanded.
Of organic EL devices, devices in which an organic material is laminated by vacuum deposition can successfully achieve high luminance light emission, however, in view of simplification of the production process, workability and the like or for obtaining a large area, the device is preferably fabricated by a coating method. The devices fabricated by the conventional coating method are, however, inferior in the luminance of emitted light and the light emission efficiency to the devices fabricated by the deposition method. Thus, improvements are still in need for attaining high luminance and highly efficient light emission.
A first object of the present invention is to provide an organic EL device using a red fluorescent dye capable of emitting red light in high color purity and having excellent durability.
A second object of the present invention is to provide a red fluorescent dye which can be used in an organic EL device, emits red light in high color purity and has excellent durability.
A third object of the present invention is to provide an organic EL device which can ensure high luminance and highly efficient light emission even when the device is fabricated by a coating method.
A fourth object of the present invention is to provide an organic EL device using a fluorescent dye capable of emitting light in the blue green area and having excellent durability.
The present invention provides the following electroluminescence devices and fluorescent dyes and thereby the above-described objects of the present invention can be attained.
[1] An organic electroluminescence device comprising at least one organic thin film between electrodes, which contains at least one compound represented by the following formula (1), (2) or (3): 
wherein X11 represents an oxygen atom, a sulfur atom or Nxe2x80x94R19, and R11 to R18 and R19, which may be the same or different, each represents a hydrogen atom or a substituent, provided that R16 and R17 are not combined to form an aromatic ring; 
wherein X21 represents an oxygen atom, a sulfur atom or Nxe2x80x94R2b, Y21 represents an oxygen atom or a sulfur atom, and R21 to R29 and R2b, which may be the same or different, each represents a hydrogen atom or a substituent, and R2a represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an unsubstituted amino group, an acylamino group, a sulfonyl-amino group, a carbamoylamino group, a sulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a phosphoramido group, an acyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, a cyano group or a halogen atom, provided that when X21 represents an oxygen atom and R29 represents a hydrogen atom, at least one of R26 to R29 represents an unsubstituted or substituted amino group; 
wherein X31, represents an oxygen atom, a sulfur atom or Nxe2x80x94R3b, Z31, represents NR31R32 or OG31, R31 to R36 and R3b each represents a hydrogen atom or a substituent, and G31 represents a hydrogen atom, a substituent or a counter cation group.
[2] A cyclic azine compound having a structure represented by the following formula (4): 
wherein X41 represents an oxygen atom, a sulfur atom or Nxe2x80x94R4b, R4b represents a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R4, and R42 each represents a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or an aryl group having from 6 to 20 carbon atoms, R43, R44 and R45 each represents a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a halogen atom, a hydroxy group, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted amino group, a substituted amino group having from 1 to 20 carbon atoms, the substituted amino group being an alkylamino group, an arylamino group, a sulfonamido group, a carbonamido group, a ureido group, a urethane group, a carbamoylamino group or a sulfamoylamino group, R46, R47, R48 and R49 each represents a hydrogen atom, a halogen atom, a substituted carbonyl group having from 1 to 30 carbon atoms, an alkylamino group having from 1 to 30 carbon atoms, an arylamino group having from 6 to 30 carbon atoms a sulfonylamino group having from 1 to 30 carbon atoms, an acylamino group having from 2 to 30 carbon atoms, a ureido group having from 1 to 30 carbon atoms, an alkoxycarbonylamino group having from 2 to 30 carbon atoms, an aryloxycarbonylamino group having from 7 to 30 carbon atoms, a carbamoylamino group having from 1 to 30 carbon atoms or a sulfamoylamino group having from 1 to 30 carbon atoms, and R4a represents a hydrogen atom, a cyano group, a substituted carbonyl group having from 1 to 30 carbon atoms, a sulfamoyl group having from 0 to 30 carbon atoms, a sulfonyl group having from 1 to 30 carbon atoms, a sulfonamido group having from 1 to 30 carbon atoms, a carbonamido group having from 1 to 30 carbon atoms or a ureido group having from 1 to 30 carbon atoms, provided that when X41 is an oxygen atom and R4a, represents a hydrogen atom or a cyano group, at least one of R46 to R49 represents a substituted amino group and when X41 represents a sulfur atom, R4a represents a hydrogen atom, a cyano group or a sulfamoyl group, the substituent of the substituted carbonyl group being an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an arylamino group or an alkylamino group.
[3] An organic electroluminescence device comprising a pair of electrodes having formed therebetween a light emitting layer or a plurality of organic compound thin films including a light emitting layer, wherein at least one layer is a layer comprising a polymer having dispersed therein a compound represented by formula (1), (2), (3) or (4) described in the above items [1] and [2].
[4] An organic electroluminescence device comprising a pair of electrodes having formed therebetween a light emitting layer or a plurality of organic compound thin film including a light emitting layer, wherein at least one layer is a layer formed by coating a compound represented by formula (1), (2), (3) or (4) described in the above items [1] and [2] or a material containing the compound.
[5] A process for producing a cyclic azine dye represented by the following formula (15), comprising reacting a phenylenediamine derivative represented by the following formula (13) with a phenol derivative represented by the following formula (14) in the presence of an oxidizing agent in an alkaline atmosphere: 
wherein X131, represents an oxygen atom, a sulfur atom or Nxe2x80x94R139, R131 to R135 and R139, which may be the same or different, each represents a hydrogen atom or a substituent, R136 to R138, which may be the same or different, each represents a hydrogen atom or a substituent, and Y131 to Y134, which may be the same or different, each represents a hydrogen atom or a splitting-off group.
[6] A process for producing a cyclic azine dye represented by the following formula (18), comprising oxidation reacting an aniline derivative represented by formula (16) or (17) by an oxidizing agent in an alkaline atmosphere: 
wherein X161 represents an oxygen atom, a sulfur atom or Nxe2x80x94R169, R161 to R168 and R169, which may be the same or different, each represents a hydrogen atom or a substituent, X171 represents an oxygen atom, a sulfur atom or Nxe2x80x94R179, R171 to R178 and R179, which may be the same or different each represents a hydrogen atom or a substituent, and Y161 to Y163 and Y171 to Y173, which may be the same or different, each represents a hydrogen atom or a splitting-off group.
[7] A process for producing a cyclic azine dye represented by formula (3), comprising reacting a carbonyl compound derivative represented by the following formula (19) with an aniline compound derivative represented by the following formula (20) or a salt thereof in the presence of an oxidizing agent in an alkaline atmosphere: 
wherein X201 represents an oxygen atom, a sulfur atom or  greater than NR192, R192 represents a hydrogen atom or a substituent, R191 represents a hydrogen atom or a substituent, Y191 and Y192, which may be the same or different, each represents a hydrogen atom or a splitting-off group, Z191 represents xe2x80x94NR193R194 or xe2x80x94OG191, R193 and R194, which may be the same or different, each represents a hydrogen atom or a substituent, G191 represents a hydrogen atom, a substituent or a counter cation group, R195 represents a substituent, and n3 represents 0 or an integer of from 1 to 3, provided that when n3 is 2 or 3, the plurality of R195 groups may be the same or different.
The present invention is described in detail below.
Formula (1) is described below. X11 represents an oxygen atom, a sulfur atom or Nxe2x80x94R19, preferably an oxygen atom or Nxe2x80x94R19. R19 represents a hydrogen atom or a substituent.
Examples of the substituent include an alkyl group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 12 carbon atoms, still more preferably from 1 to 8 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl and cyclohexyl; an alkenyl group preferably having from 2 to 20 carbon atoms, more preferably from 2 to 12 carbon atoms, still more preferably from 2 to 8 carbon atoms, such as vinyl, allyl, 2-butenyl and 3-pentenyl; an alkynyl group preferably having from 2 to 20 carbon atoms, more preferably from 2 to 12 carbon atoms, still more preferably from 2 to 8 carbon atoms, such as propargyl and 3-pentynyl; an aryl group preferably having from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, still more preferably from 6 to 12 carbon atoms, such as phenyl, p-methylphenyl and naphthyl; an acyl group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl and pivaloyl; an alkoxycarbonyl group preferably having from 2 to 20 carbon atoms, more preferably from 2 to 16 carbon atoms, still more preferably from 2 to 12 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; an aryloxycarbonyl group preferably having from 7 to 20 carbon atoms, more preferably from 7 to 16 carbon atoms, still more preferably from 7 to 10 carbon atoms, such as phenyloxycarbonyl; an alkylaminocarbonyl group preferably having from 1 to 40 carbon atoms, more preferably from 1 to 30 carbon atoms, still more preferably from 1 to 25 carbon atoms, such as ethylaminocarbonyl and dimethylaminocarbonyl; an arylaminocarbonyl group preferably having from 7 to 40 carbon atoms, more preferably from 7 to 30 carbon atoms, still more preferably from 7 to 10 carbon atoms, such as phenylaminocarbonyl; a sulfonyl group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12 carbon atoms, such as mesyl and tosyl; and a heterocyclic group, preferably a heterocyclic group having a 5- or 6-membered monocyclic or condensed ring structure and having from 3 to 30 carbon atoms (the hetero atom is, for example, oxygen, nitrogen or sulfur), such as imidazolyl, pyridyl, furyl, piperidyl and morpholino.
These substituents each may further be substituted.
R19 may be combined with R13 or R18 to form a 5- or 6-membered nitrogen-containing heterocyclic ring having from 3 to 20 carbon atoms.
R19 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 1 to 20 carbon atoms. The substituent of the substituted carbonyl group is an aliphatic group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an unsubstituted or substituted amino group or a hydroxyl group. The substituent of the substituted sulfonyl group is an aliphatic group, an aryl group, an alkoxy group, a substituted or unsubstituted amino group or a hydroxyl group. The substituted amino group is an alkylamino group, an arylamino group, a sulfonamido group, a carbonamido group, a ureido group, a urethane group, a carbamoylamino group or a sulfamoylamino group. R19 is particularly preferably a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms.
R11 to R18, which may be the same or different, each represents a hydrogen atom or a substituent.
Examples of the substituents of R11 and R12 include the substituents described above for R19.
Examples of the substituent of R13 to R18 include an alkyl group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, 2-ethylhexyl, cyclopentyl, cyclohexyl, trifluoromethyl, pentafluoromethyl), an alkenyl group (preferably having from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, still more preferably from 2 to 12 carbon atoms, e.g., vinyl, allyl, 2-butenyl, 3-pentenyl), an alkynyl group (preferably having from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, still more preferably from 2 to 12 carbon atoms, e.g., propargyl, 3-pentynyl), an aryl group (preferably having from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, still more preferably from 6 to 12 carbon atoms, e.g., phenyl, p-methylphenyl, naphthyl, pentafluorophenyl), an unsubstituted amino group, an alkyl-substituted or aryl-substituted amino group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., amino, methylamino, dimethylamino, diethylamino, dibenzylamino, anilino), an alkoxy group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., methoxy, ethoxy, butoxy), an aryloxy group (preferably having from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, still more preferably from 6 to 12 carbon atoms, e.g., phenyloxy, 2-naphthyloxy), an acyl group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably having from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, still more preferably from 2 to 12 carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl), an aryloxycarbonyl group (preferably having from 7 to 30 carbon atoms, more preferably from 7 to 20 carbon atoms, still more preferably from 7 to 12 carbon atoms, e.g., phenyloxycarbonyl), an alkylaminocarbonyl group (preferably having from 2 to 40 carbon atoms, more preferably from 2 to 30 carbon atoms, still more preferably from 2 to 25 carbon atoms, e.g., ethylaminocarbonyl, dimethylaminocarbonyl), an arylaminocarbonyl group (preferably having from 7 to 40 carbon atoms, more preferably from 7 to 30 carbon atoms, still more preferably from 7 to 12 carbon atoms, e.g., phenylaminocarbonyl), an acyloxy group (preferably having from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, still more preferably from 2 to 12 carbon atoms, e.g., acetoxy, benzoyloxy), an acylamino group (preferably having from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, still more preferably from 2 to 12 carbon atoms, e.g., acetylamino, benzoylamino), an alkoxycarbonylamino group (preferably having from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, still more preferably from 2 to 12 carbon atoms, e.g., methoxycarbonylamino), an aryloxycarbonylamino group (preferably having from 7 to 30 carbon atoms, more preferably from 7 to 20 carbon atoms, still more preferably from 7 to 12 carbon atoms, e.g., phenyloxycarbonylamino), a sulfonylamino group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon toms, e.g., methane-sulfonylamino, benzenesulfonylamino), a sulfamoyl group (preferably having from 0 to 30 carbon atoms, more preferably from 0 to 20 carbon atoms, still more preferably from 0 to 12 carbon atoms, e.g., sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl), a carbamoyl group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl), a carbamoylamino group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., carbamoylamino, ethylcarbamoylamino, dimethylcarbamoylamino, phenylcarbamoylamino), a sulfamoylamino group (preferably having from 0 to 30 carbon atoms, more preferably from 0 to 20 carbon atoms, still more preferably from 0 to 12 carbon atoms, e.g., sulfamoylamino, methylsulfamoylamino, diethylsulfamoylamino, phenylsulfamoylamino), an alkylthio group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., methylthio, ethylthio), an arylthio group (preferably having from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, still more preferably from 6 to 12 carbon atoms, e.g., phenylthio), a sulfonyl group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., mesyl, tosyl), a sulfinyl group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., methanesulfinyl, benzenesulfinyl), a ureido group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., ureido, methylureido, phenylureido), a phosphoramido group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 12 carbon atoms, e.g., diethylphosphoramido, phenylphosphoramido), a hydroxy group, a mercapto group, a halogen atom (e.g., fluorine, chlorine, bromine, iodine), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group and a heterocyclic group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms; the hetero atom is, for example, a nitrogen atom, an oxygen atom or a sulfur atom; specific examples include imidazolyl, benzimidazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, pyridyl, furyl, piperidyl and morpholino). These substituents each may further be substituted.
Any of the substituents R13 to R18 may be combined to form a 5- or 6-membered alicyclic, heterocyclic or aromatic ring, provided that R16 and R17 are not combined to form an aromatic ring.
R11 and R12 each is preferably a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or an aryl group having from 6 to 20 carbon atoms. R11 and R12 may combine with R13 or R14, respectively, to form a 5- or 6-membered alicyclic ring, for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring. R11 and R12 may be combined to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring.
R13, R14 and R15 each is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a halogen atom, a hydroxy group, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted amino group or a substituted amino group having from 1 to 20 carbon atoms. The substituted amino group is an alkylamino group, an arylamino group, an aromatic heterocyclic amino group, a sulfonamido group, a carbonamido group, a ureido group, a urethane group, a carbamoylamino group or a sulfamoylamino group.
R13, R14 and R15 each is more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 10 carbon atoms or a substituted amino group having from 1 to 10 carbon atoms. The substituted amino group is an alkylamino group, an arylamino group, an aromatic heterocyclic amino group, a sulfonamido group, a carbonamido group, a ureido group, a urethane group, a carbamoylamino group or a sulfamoylamino group.
R16 and R17 each is preferably a hydrogen atom, a halogen atom, a sulfonamido group having from 1 to 30 carbon atoms, a carbonamido group having from 1 to 30 carbon atoms or a ureido group having from 1 to 30 carbon atoms. R18 is preferably a hydrogen atom, a halogen atom, a cyano group, an alkyl group having from 1 to 30 carbon atoms, an aryl group having from 6 to 30 carbon atoms, a heterocyclic group having from 2 to 30 carbon atoms, a substituted carbonyl group having from 1 to 30 carbon atoms, a sulfamoyl group having from 0 to 30 carbon atoms, a sulfonamido group having from 1 to 30 carbon atoms, a carbonamido group having from 1 to 30 carbon atoms or a ureido group having from 1 to 30 carbon atoms, more preferably a hydrogen atom, a halogen atom, a substituted carbonyl group having from 1 to 30 carbon atoms or an amido group having from 1 to 30 carbon atoms.
The preferred combination in formula (1) is described below.
In formula (1), preferred is the combination such that X11 is an oxygen atom or Nxe2x80x94R19, R19 is a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, the substituent of the substituted carbonyl group is an aliphatic group, an aryl group, a heterocyclic group, an alkoxy group or an aryloxy group, the substituent of the substituted sulfonyl group is an aliphatic group or aryl group, R11 and R12 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an aryl group having from 6 to 20 carbon atoms and may combine with R13 or R14, respectively to form a ring (preferably a 5- or 6-membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring, or R11 and R12 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R13, R14 and R15 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a halogen atom or a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, R16 and R17 each is a hydrogen atom, a halogen atom, a sulfonylamino group having from 1 to 20 carbon atoms, an acylamino group having from 2 to 20 carbon atoms or an ureido group having from 1 to 20 carbon atoms, and R1 is a hydrogen atom, a halogen atom, a cyano group, a substituted carbonyl group having from 1 to 20 carbon atoms, a sulfamoyl group having from 0 to 20 carbon atoms, a sulfonylamino group having from 1 to 20 carbon atoms, an acylamino group having from 1 to 20 carbon atoms or a ureido group having from 1 to 20 carbon atoms.
Formula (2) is described below.
X21 represents an oxygen-atom, a sulfur atom or Nxe2x80x94R2b, preferably an oxygen atom or Nxe2x80x94R2b. Examples and preferred range of R2b are the same as those of R19 in formula (1). Y21 represents an oxygen atom or a sulfur atom, preferably an oxygen atom. Examples and preferred range of R21 to R25 are the same as those of R11 to R15 in formula (1). Examples of the substituent of R26 to R29 are the same as those of the substituent of R13 to R18 in formula (1). R26 to R29 each is preferably a hydrogen atom, a halogen atom, a substituted carbonyl group having from 1 to 30 carbon atoms, an alkylamino group having from 1 to 30 carbon atoms, an arylamino group having from 6 to 30 carbon atoms, a sulfonylamino group having from 1 to 30 carbon atoms, an acylamino group having from 2 to 30 carbon atoms, a ureido group having from 1 to 30 carbon atoms, an alkoxycarbonylamino group having from 2 to 30 carbon atoms, an aryloxycarbonylamino group having from 7 to 30 carbon atoms, a carbamoylamino group having from 1 to 30 carbon atoms or a sulfamoylamino group having from 1 to 30 carbon atoms. Examples of the substituent of the substituted carbonyl group include an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an arylamino group and an alkylamino group. R26 to R29 each is more preferably a hydrogen atom, an acylamino group having from 1 to 20 carbon atoms, a ureido group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms or an aryloxycarbonylamino group having from 7 to 20 carbon atoms. Still more preferably, either one of R26 and R29 is an acylamino group having from 1 to 20 carbon atoms, a ureido group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms or an aryloxycarbonylamino group having from 7 to 20 carbon atoms.
R2a represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an unsubstituted amino group, an acylamino group, a sulfonylamino group, a carbamoylamino group, a sulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a phosphoramido group, an acyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, a cyano group or a halogen atom, preferably a hydrogen atom, a heterocyclic group, an unsubstituted amino group, an acylamino group, a sulfonylamino group, a carbamoylamino group, a sulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, an acyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, a cyano group or a halogen atom, still more preferably a hydrogen atom, an acylamino group, a sulfonylamino group, a carbamoylamino group, a sulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, an acyl group, a carbamoyl group or a cyano group.
In formula (2), preferred is the combination such that X21 is an oxygen atom or Nxe2x80x94R2b, R2b is a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, the substituent of the substituted carbonyl group is an aliphatic group, an aryl group, a heterocyclic group, an alkoxy group or an aryloxy group, the substituent of the substituted sulfonyl group is an aliphatic group or an aryl group, Y21 is an oxygen atom, R21 and R22 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R23 or R24, respectively, to form a ring (preferably, a 5- or 6-membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring, or R21 and R22 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R23, R24 and R25 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, R26 to R29 each is a hydrogen atom, a sulfonylamino group having from 1 to 20 carbon atoms, an acylamino group having from 2 to 20 carbon atoms, a ureido group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms, an aryloxycarbonylamino group having from 7 to 20 carbon atoms, a carbamoylamino group having from 1 to 20 carbon atoms or a sulfamoylamino group having from 1 to 20 carbon atoms, and R2a is a hydrogen atom, a heterocyclic group having from 2 to 20 carbon atoms, an unsubstituted amino group, an acylamino group having from 2 to 20 carbon atoms, a sulfonylamino group having from 1 to 20 carbon toms, a carbamoylamino group having from 1 to 20 carbon atoms, a sulfamoylamino group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms, an aryloxycarbonylamino group having from 7 to 20 carbon atoms, an acyl group having from 2 to 20 carbon atoms, a carbamoyl group having from 1 to 20 carbon atoms, a sulfonyl group having from 1 to 20 carbon atoms, a sulfamoyl group having from 1 to 20 carbon atoms, a cyano group or a halogen atom, provided that when X21 is an oxygen atom and R2a is a hydrogen atom, at least one of R26 to R29 is an unsubstituted or substituted amino group.
Formula (3) is described below.
X31 represents an oxygen atom, a sulfur atom or Nxe2x80x94R3b, preferably an oxygen atom or Nxe2x80x94R3b. Examples and preferred range of R3b are the same as those of R19 in formula (1). Z31 represents NR31R32 or OG31. Examples and preferred range of R31 to R35 are the same as those of R11 to R15 in formula (1).
R36 represents a hydrogen atom or a substituent.
Examples of the substituent are set forth below, however, the present invention is by no means limited thereto:
an alkyl group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 12 carbon atoms, still more preferably from 1 to 8 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl and cyclohexyl;
an alkenyl group preferably having from 2 to 20 carbon atoms, more preferably from 2 to 12 carbon atoms, still more preferably from 2 to 8 carbon atoms, such as vinyl, allyl, 2-butenyl and 3-pentenyl;
an alkynyl group preferably having from 2 to 20 carbon atoms, more preferably from 2 to 12 carbon atoms, still more preferably from 2 to 8 carbon atoms, such as propargyl and 3-pentynyl;
an aryl group preferably having from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, still more preferably from 6 to 12 carbon atoms, such as phenyl, p-methylphenyl and naphthyl;
a substituted carbonyl group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12 carbon atoms, such as acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl and phenylaminocarbonyl;
a substituted amino group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12 carbon atoms, such as dimethylamino, methylcarbamoyl, ethylsulfonylamino, dimethylaminocarbonylamino and phthalimido;
a sulfonyl group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12 carbon atoms, such as mesyl and tosyl;
a heterocyclic group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12 carbon atoms (the hetero atom is, for example, oxygen, nitrogen or sulfur), such as imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl and triazolyl;
an alkoxy group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12 carbon atoms, such as methoxy and benzyloxy;
an aryloxy group preferably having from 6 to 20 carbon atoms, more preferably from 6 to 16 carbon atoms, still more preferably from 6 to 12 carbon atoms, such as phenoxy and naphthyloxy;
a halogen atom, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
an alkylthio group preferably having from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12 carbon atoms, such as methylthio;
an arylthio group preferably having from 6 to 20 carbon atoms, more preferably from 6 to 16 carbon atoms, still more preferably from 6 to 12 carbon atoms, such as phenylthio; and additionally
a sulfo group, a carboxyl group, a hydroxyl group, a thiol group and a cyano group.
These substituents each may further be substituted.
R36 is preferably a cyano group, a substituted or unsubstituted aryl group, an aromatic heterocyclic group (for example, a substituted or unsubstituted benzazole group (e.g., benzoxazolyl) or a triazolyl group), a substituted carbonyl group (for example, a phenylaminocarbonyl group, a methoxycarbonyl group or t-butylcarbonyl group) or a substituted sulfonyl group (for example, a methanesulfonyl group). R36 is more preferably a cyano group, a substituted or unsubstituted benzazole group (e.g., benzoxazolyl) or a substituted carbonyl group, still more preferably a substituted or unsubstituted benzazole group (e.g., benzoxazolyl) or a substituted carbonyl group.
G31 represents a hydrogen atom, a substituent or a counter cation. Examples of the substituent include the substituents described above for R3b. The counter cation is not particularly limited, however, examples thereof include a metal cation (e.g., lithium ion, sodium ion, aluminum ion, europium ion) and a quaternary ammonium ion (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 10 carbon atoms, e.g., tetrabutylammonium ion). The metal cation may have a ligand.
G31 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group (preferably having from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, still more preferably from 1 to 10 carbon atoms, e.g., methyl, isopropyl, methoxyethoxymethyl), a substituted or unsubstituted aryl group (preferably having from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, still more preferably from 6 to 10 carbon atoms, e.g., phenyl, p-methoxyphenyl), an alkali metal ion, an alkaline earth metal ion, an aluminum ion, a zinc ion, a europium ion, a borate ion or a quaternary ammonium ion.
G31 is more preferably a hydrogen atom, a substituted or unsubstituted alkyl group, an alkali metal ion or a quaternary ammonium ion, still more preferably a hydrogen atom or a substituted or unsubstituted alkyl group.
Formula (4) is described-below.
The compound represented by formula (4) is included in the compound represented by formula (2).
The compound of formula (4) is preferably represented by the following formula (5), (6), (7), (8) or (9): 
In formula (5), preferred is the combination such that X51 is an oxygen atom, a sulfur atom or Nxe2x80x94R5b, R5b is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R51 and R52 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R53 or R54, respectively, to form a ring (preferably a 5- or 6-membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring, or R51 and R52 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R53, R54 and R55 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a halogen atom, a hydroxy group, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms or an unsubstituted amino group or a substituted amino group having from 1 to 20 carbon atoms, R56 to R59 each is a hydrogen tom, a halogen atom, a substituted carbonyl group having from 1 to 30 carbon atoms, an alkylamino group having from 1 to 30 carbon atoms, an arylamino group having from 6 to 30 carbon atoms, a sulfonylamino group having from 1 to 30 carbon atoms, an acylamino group having from 2 to 30 carbon atoms, a ureido group having from 1 to 30 carbon atoms, an alkoxycarbonylamino group having from 2 to 30 carbon atoms, an aryloxycarbonylamino group having from 7 to 30 carbon atoms, a carbamoylamino group having from 1 to 30 carbon atoms or a sulfamoylamino group having from 0 to 30 carbon atoms, provided that at least one of R56 to R59 is an unsubstituted or substituted amino group, and R5a is a hydrogen atom or a cyano group.
More preferred is the combination such that X51 is an oxygen atom or Nxe2x80x94R5b, R5b is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R51 and R52 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R53 or R54, respectively, to form a ring (preferably a 5- or 6-memered alicyclic ring), for example, an indole ring, a quinoline ring or a Julolidine ring, or R51 and R52 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R53, R54 and R55 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, R56 to R59 each is a hydrogen atom, a sulfonylamino group having from 1 to 20 carbon atoms, an acylamino group having from 2 to 20 carbon atoms, a ureido group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms, an aryloxycarbonylamino group having from 7 to 20 carbon atoms, a carbamoylamino group having from 1 to 20 carbon atoms or a sulfamoylamino group having from 1 to 20 carbon atoms, provided that at least one of R56 to R59 is an acylamino group having from 2 to 20 carbon atoms, a sulfonylamino group having from 1 to 20 carbon atoms, a ureido group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms, an aryloxycarbonylamino group having from 7 to 20 carbon atoms, a carbamoylamino group having from 1 to 20 carbon atoms or a sulfamoylamino group having from 0 to 20 carbon atoms, and R5a is a hydrogen atom or a cyano group.
Still more preferred is the combination such that X51 is an oxygen atom or Nxe2x80x94R5b, R5b is a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, R51 and R52 each is a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 12 carbon atoms and may combine with R53 or R54, respectively, to form a ring or R51 and R52 may be combined with each other to form a ring, R53, R54 and R55 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 12 carbon atoms, R56 to R59 each is a hydrogen atom, a sulfonylamino group having from 1 to 12 carbon atoms, an acylamino group having from 2 to 12 carbon atoms, a ureido group having from 1 to 12 carbon atoms, an alkoxycarbonylamino group having from 2 to 12 carbon atoms, an aryloxycarbonylamino group having from 7 to 12 carbon atoms, preferably, either one of R56 and R59 is a sulfonamido group having from 1 to 12 carbon atoms, a carbonamido group having from 2 to 12 carbon atoms, a ureido group having from 1 to 12 carbon atoms, an alkoxycarbonylamino group having from 2 to 12 carbon atoms or an aryloxycarbonylamino group having from 7 to 12 carbon atoms and the others each is a hydrogen atom, and R5a is a hydrogen atom or a cyano group. 
In formula (6), preferred is the combination such that X61 is an oxygen atom or Nxe2x80x94R6c, R6c is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R61 and R62 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R63 or R64, respectively, to form a ring (preferably, a 5- or 6-membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring or R61 and R62 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R63, R64 and R65 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a halogen atom, a hydroxy group, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted amino group or a substituted amino group having from 1 to 20 carbon atoms, R66 to R69 each is a hydrogen atom, a halogen atom, a substituted carbonyl group having from 1 to 30 carbon atoms, an alkylamino group having from 1 to 30 carbon atoms, an arylamino group having from 1 to 30 carbon atoms, a sulfonylamino group having from 1 to 30 carbon atoms, an acylamino group having from 2 to 30 carbon atoms, a ureido group having from 1 to 30 carbon atoms, an alkoxycarbonylamino group having from 2 to 30 carbon atoms, an aryloxycarbonylamino group having from 7 to 30 carbon atoms, a carbamoylamino group having from 1 to 30 carbon atoms or a sulfamoylamino group having from 0 to 30 carbon atoms, and R6a and R6b each is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heterocyclic oxycarbonyl group, a sulfonyl group, a carbamoyl group or a sulfamoyl group, provided that R6a or R6b is not combined with any one of R61 to R69 to form a ring.
More preferred is the combination such that X61 is an oxygen atom or Nxe2x80x94R6c, R6c is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R61 and R62 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R63 or R64, respectively, to form a ring (preferably, a 5- or 6-membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring or R61 and R62 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R63, R64 and R65 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, R66 to R69 each is a hydrogen atom, a sulfonylamino group having from 1 to 20 carbon atoms, an acylamino group having from 2 to 20 carbon atoms, a ureido group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms, an aryloxycarbonylamino group having from 7 to 20 carbon atoms, a carbamoylamino group having from 1 to 20 carbon atoms or a sulfamoylamino group having from 0 to 20 carbon atoms, and R6a and R6b each is a hydrogen atom, an acyl group having from 1 to 20 carbon atoms, a sulfonyl group having from 1 to 20 carbon atoms, a carbamoyl group having from 1 to 20 carbon atoms, a Sulfamoyl group having from 0 to 20 carbon atoms or an alkoxycarbonyl group having from 2 to 20 carbon atoms, provided that R6a or R6b is not combined with any one of R61 to R69 to form a ring.
Still more preferred is the combination such that X61 is an oxygen atom or Nxe2x80x94R6c, R6c is a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, R61 and R62 each is a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 12 carbon atoms and may combine with R63 or R64, respectively, to form a ring or R61 and R2 may be combined with each other to form a ring, R63, R64 and R65 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 12 carbon atoms, R66 to R69 each is a hydrogen atom, a sulfonylamino group having from 1 to 12 carbon atoms, an acylamino group having from 2 to 12 carbon atoms, a ureido group having from 1 to 12 carbon atoms, an alkoxycarbonylamino group having from 2 to 12 carbon atoms or an aryloxycarbonylamino group having from 7 to 12 carbon atoms, and R6a and R6b each is a hydrogen atom, an acyl group having from 1 to 12 carbon atoms, a sulfonyl group having from 1 to 12 carbon atoms, a carbamoyl group having from 1 to 12 carbon atoms, a sulfamoyl group having from 0 to 12 carbon atoms or an alkoxycarbonyl group having from 2 to 12 carbon atoms, provided that R6a or R6b is not combined with any one of R61 to R69 to form a ring. 
In formula (7), preferred is the combination such that X71 is an oxygen atom or Nxe2x80x94R7b, R7b is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R71 and R72 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R73 or R74, respectively, to form a ring (preferably, a 5- or 6-membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring or R71 and R72 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R73, R74 and R75 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a halogen atom, a hydroxy group, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted amino group or a substituted amino group having from 1 to 20 carbon atoms, R76 to R79 each is a hydrogen atom, a halogen atom, a substituted carbonyl group having from 1 to 30 carbon atoms, an alkylamino group having from 1 to 30 carbon atoms, an arylamino group having from 6 to 30 carbon atoms, a sulfonylamino group having from 1 to 30 carbon atoms, an acylamino group having from 2 to 30 carbon atoms, a ureido group having from 1 to 30 carbon atoms, an alkoxycarbonylamino group having from 2 to 30 carbon atoms, an aryloxycarbonylamino group having from 7 to 30 carbon atoms, a carbamoylamino group having from 1 to 30 carbon atoms or a sulfamoylamino group having from 0 to 30 carbon atoms, and R7a is an aryl group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an unsubstituted or substituted amino group or a hydroxy group.
More preferred is the combination such that X71 is an oxygen atom or Nxe2x80x94R7b, R7b is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R71 and R72 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R73 or R74, respectively, to form a ring (preferably, a 5- or 6-membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring or R71 and R72 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R73, R74 and R75 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, R76 to R79 each is a hydrogen atom, a sulfonylamino group having from 1 to 20 carbon atoms, an acylamino group having from 2 to 20 carbon atoms, a ureido group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms, an aryloxycarbonylamino group having from 7 to 20 carbon atoms, a carbamoylamino group having from 1 to 20 carbon atoms or a sulfamoylamino group having from 0 to 20 carbon atoms, and R7a is an aryl group having from 6 to 20 carbon atoms, an unsubstituted amino group or a substituted amino group having from 1 to 20 carbon atoms.
Still more preferred is the combination such that X71 is an oxygen atom or Nxe2x80x94R7b, R7b is a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, R71 and R72 each is a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 12 carbon atoms and may combine with R73 or R74, respectively, to form a ring or R71 and R72 may be combined with each other to form a ring, R73, R74 and R75 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 12 carbon atoms, R76 to R79 each is a hydrogen atom, a sulfonylamino group having from 1 to 12 carbon atoms, an acylamino group having from 2 to 12 carbon atoms, a ureido group having from 1 to 12 carbon atoms, an alkoxycarbonylamino group having from 2 to 12 carbon atoms or an aryloxycarbonylamino group having from 7 to 12 carbon atoms, and R7a is a substituted or unsubstituted amino group having from 1 to 12 carbon atoms, particularly preferably a substituted amino group in which the substituent is an alkyl group having from 1 to 12 carbon atoms or an aryl group having from 6 to 12 carbon atoms. 
In formula (8), preferred is the combination such that X81 is an oxygen atom, a sulfur atom or Nxe2x80x94R8b, R8b is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R81 and R82 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R83 or R84, respectively, to form a ring (preferably, a 5- or 6-membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring or R81 and R82 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R83, R84 and R85 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a halogen atom, a hydroxy group, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted amino group or a substituted amino group having from 1 to 20 carbon atoms, R86 to R89 each is a hydrogen atom, a halogen atom, a substituted carbonyl group having from 1 to 30 carbon atoms, an alkylamino group having from 1 to 30 carbon atoms, an arylamino group having from 6 to 30 carbon atoms, a sulfonylamino group having from 1 to 30 carbon atoms, an acylamino group having from 2 to 30 carbon atoms, a ureido group having from 1 to 30 carbon atoms, an alkoxycarbonylamino group having from 2 to 30 carbon atoms, an aryloxycarbonylamino group having from 7 to 30 carbon atoms, a carbamoylamino group having from 1 to 30 carbon atoms or a sulfamoylamino group having from 0 to 30 carbon atoms, and R8a is an aliphatic group, an aryl group, an alkoxy group, a substituted or unsubstituted amino group or a hydroxy group.
More preferred is the combination such that X81 is an oxygen atom or Nxe2x80x94R8b, R8b is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R81 and R82 each is an unsubstituted or substituted alkyl group having from 1 to 20 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 20 carbon atoms and may combine with R83 or R84, respectively, to form a ring (preferably, a 5- or 6 membered alicyclic ring), for example, an indoline ring, a tetrahydroquinoline ring or a Julolidine ring or R81 and R82 may be combined with each other to form a ring, for example, a pyrrolidine ring, a piperidine ring or a morpholine ring, R83, R84 and R85 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, R86 to R89 each is a hydrogen atom, a sulfonylamino group having from 1 to 20 carbon atoms, an acylamino group having from 2 to 20 carbon atoms, a ureido group having from 1 to 20 carbon atoms, an alkoxycarbonylamino group having from 2 to 20 carbon atoms, an aryloxycarbonylamino group having from 7 to 20 carbon atoms, a carbamoylamino group having from 1 to 20 carbon atoms or a sulfamoylamino group having from 0 to 20 carbon atoms, and R8a is an alkyl group having from 1 to 20 carbon atoms, an alkenyl group, an alkynyl group, an aryl group having from 6 to 20 carbon atoms, an alkoxy group having from 1 to 20 carbon atoms, an unsubstituted amino group or a substituted amino group having from 1 to 20 carbon atoms.
Still more preferred is the combination such that X81 is an oxygen atom or Nxe2x80x94R8b, R8b is a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, R81 and R82 each is a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms or an unsubstituted or substituted aryl group having from 6 to 12 carbon atoms and may combine with R83 or R84, respectively, to form a ring or R81 and R82 may be combined with each other to form a ring, R83, R84 and R85 each is a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms or a substituted or unsubstituted alkoxy group having from 1 to 12 carbon atoms, R86 to R89 each is a hydrogen atom, a sulfonylamino group having from 1 to 12 carbon atoms, an acylamino group having from 2 to 12 carbon atoms, a ureido group having from 1 to 12 carbon atoms, an alkoxycarbonylamino group having from 2 to 12 carbon atoms or an aryloxycarbonylamino group having from 7 to 12 carbon atoms, and R8a is an alkyl group having from 1 to 12 carbon atoms, an alkenyl group, an alkynyl group, an aryl group having from 6 to 12 carbon atoms, a substituted or unsubstituted amino group having from 1 to 12 carbon atoms, particularly preferably a substituted amino group having from 1 to 12 carbon atoms in which the substituent is an alkyl group having from 1 to 12 carbon atoms or an aryl group having from 6 to 12 carbon atoms.
The compounds represented by formulae (1) to (4) each may be a low molecular weight compound. A high molecular weight compound (preferably having a weight-average molecular weight of from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, still more preferably from 10,000 to 1,000,000) where a residue represented by formula (1), (2), (3) or (4) is connected to the polymer main chain or a high molecular weight compound (preferably having a weight-average molecular weight of from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, still more preferably from 10,000 to 1,000,000) having a skeleton of formula (1), (2), (3) or (4) in the main chain may also be used. In the case of a high molecular weight compound, the compound may be either a homopolymer or a copolymer with another monomer.
The compounds represented by formulae (1) to (4) each is preferably a low molecular weight compound. For the sake of convenience, formulae (1) to (4) each is shown as a limiting structure but tautomers thereof may also be used.
Examples of the compounds represented by formulae (1) to (4) are set forth below, however, the present invention is by no means limited thereto.
Examples of the Compound of Formula (1): 
Examples of the Compounds of Formulae (2) and (4): 
Examples of the Compound of Formula (3): 
The synthesis method of the compounds of the present invention is described below. The compounds of the present invention can be synthesized by various methods, however, in general, the compounds are synthesized by a method of reacting an o-nitrosophenol with a naphthol derivative to cause cyclization and thereby synthesize the compound or a method of oxidation coupling phenylenediamine or an aminophenol with phenol, naphthol or aniline described in items ([5] to [7] above as shown in the following Synthesis Examples.
Some synthesis examples of the compounds of the present invention are described below.